Asymmetric Synthesis of D-Fucosamine and N-Methyl-D-Fucosamine

Synlett

Volumn 1997, Issue 1, 1997, Pages 83-84

  Ojea, Vicente ^a   Ruiz, María ^a   Quintela, José M ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003165041     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-696     Document Type: Article

References (25)

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2. Kennedy, J.F.; White, C.A. Bioactive Carbohydrates. In Chemistry, Biochemistry and Biology; Ellis Horwood: Chichester, 1983.
3. Aono, R.; Masakazu, U. Biochem. J. 1986, 233, 291 and references cited therein.
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7. a. Koide, Y.; Ito, A.; Ishii, F., Koyama, Y.; Edo, K.; Ishida, N. J. Antibiot. 1982, 35, 766.
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9. Myers, A.G.; Harrington, P.M.; Kwon, B.M. J. Am. Chem. Soc. 1992, 114, 1086.
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12. Sames, D.; Polt, R. J. Org. Chem. 1994, 59, 4596.
13. Ruiz, M.; Ojea, V.; Quintela, J.M. Tetrahedron Lett. 1996, 37, 5743.
14. Dondoni, A; Perrone, D.; Semola, T. Synthesis 1995, 181.
15. Servi, S. J. Org. Chem. 1985, 50, 5865.
16. Cyclo[(2S)-val-gly] was obtained as described by Rose et al. Treatment of this compound with triethyloxonium tetrafluorborate allowed the preparation of the 2,5-diethoxy pyrazine derivative. See Rose, J.E., Leeson, P.D.; Gani, D. J. Chem. Soc. Perkin Trans 1 1995, 157. Alternatively, both enantiomers of the related 2,5-dimethoxy-3-isopropyl-3,6-dihydropyrazine can be purchased from E. Merck.
17. 2Ph); 7.18-7.35 (m, 5H, ArH).
18. Prolonged reaction times or the use of ethers as the solvent resulted in a complete hydrolysis to the corresponding 2-amino-4,5-dihydroxy acid, isolated in low yields. Lactonization of this compound was not efficiently achieved.
19. Attempts to achieve the N-methylation of the benzylcarbamate 8 under several conditions (sodium hydride or potassium carbonate and methyl iodide) resulted in recovered starting material or decomposition compounds after prolonged reaction times. See also note 21.
20. Borch, R.F.; Hassid, A.I. J. Org. Chem. 1972, 37, 1673.
21. O'Donnell, M.J.; Polt, R.L. J. Org. Chem. 1982, 47, 2663.
22. 2); 7.10-7.51 (m, 15H, ArH).
23. Treatment of compound 11a with sodium hydride and methyl iodide (THF, -15°C) led to the exclusive formation of a 3-amino-5H-furan-2-one derivative (by syn elimination of the bencyloxy group at position 4) instead of the desired N-methyl derivative.
24. 2); 7.20-7.56 (m, 15H, ArH).
25. 2O)}.